Procrastination, Self Esteem and Freelance Writing

Procrastinating was my biggest problem as an attorney. I never met a deadline I couldn’t miss; even the strictest litigation deadlines were no match for my dedication to putting things off. I lived in a constant state of worry, and although I managed to avoid getting into trouble, I always expected to be called out. I hated myself for it, but no matter what I did, I couldn’t bring myself to get the work done.


Over time, I realized that my problem wasn’t so much procrastination as it was self-esteem. I never felt confident as a lawyer. I spent my final year of law school studying overseas, and as a result, I missed a lot of opportunities to intern and take clinical courses. While law school is in many ways unrelated to the practice of law, I did inadvertently miss some good opportunities to gain experience and confidence.


After law school, I went straight to the “firm” I had worked at since college. There, I had no opportunity to find a mentor, or to advance. I worked for a stereotypical attorney who expected the largest amount of money for the least amount of work. Of course, everyone wants that to some degree. But as I became more capable with the law, he started taking on clients with cases I didn’t know how to handle. I was expected to do the work on my own, with few resources available. He never took the time to teach me what he knew, and he made it clear I wasn’t to ask for outside help.


I muddled through as best I could. But in most areas of law, there is no guidebook, telling a clueless attorney exactly what to do and when to do it. When guidebooks were available, they were priced out of my reach and my employer’s willingness to pay. I researched and observed as much as possible, and I called friends and acquaintances for help far more than I felt comfortable.


With several exceptions, I never got used to flying blind. I’d panic before returning phone calls, knowing that I was about to reveal my lack of knowledge. Simple pleadings took hours as I desperately searched for forms. Court was a nightmare of startled comments from judges and mediators wondering how such a clueless lawyer ended up in front of them. I know a lot of it became exaggerated in my mind, because my clients and boss always gave me good feedback, but I was definitely not known for competence.


I am not so scared as a writer. There are technical aspects to all writing, and some forms of writing are beyond my skill level simply because I have no experience with them. But I am comfortable with the craft of writing, and with time, I know I can learn any style to at least a basic level. Right now there is plenty of work that suits my level of skill and interest. I may need to research a topic, but once I have the necessary information, I know exactly how to proceed.


I suppose I have some fears of rejection, but when it comes to writing, I am confident in my abilities. I fear edits because they are annoying, sometimes pointless, and sometimes embarrassing. But I don’t fear someone saying something negative, because I do know I can write. There may be an occasional spelling or grammatical error, especially in my own blog posts and comments, but I don’t doubt my skills. I have proven, over a lifetime of education, exams and accolades, that I know how to write well. With practice, study and training, I will become even better.


But, recently I noticed myself trying to procrastinate. And in analyzing it more, I see that once again, confidence is the culprit. Those old fears are coming back because I’m working again, and my mind somehow expects work to be miserable and scary. I’m not sure what I’m afraid of, but there’s a voice telling me that I don’t know what I’m doing. A voice tells me nobody will like my work, and I might as well not start, because I won’t know what to do.


Fortunately, I have enough experience and self-awareness to quiet that voice. I know I can write, and I know most of my clients will be happy with what I produce. If I start to panic, I only have to remind myself that my client is not expecting a dissertation or technical manual. My clients want work in the voice of me, the person they hired.

Once I remind myself of my capabilities, I find all inclination to procrastinate goes out the window. I have turned some assignments in on the due date simply because they took a long time, or the deadline was tight to begin with. But if I have free time, I find myself using it to get my work done. If I turn an article in a week early, the satisfaction of that is rewarding enough that I am motivated to keep working.


To me, there is no better feeling than being able to work with a deadline. No longer do I have that dread and shame hanging over my head. Instead, I’m in a career that suits my skills, and I believe in my abilities. I can quiet that voice of doubt because I do know what to do. Just sit down and write, that’s all there is to it.

Nobody is immune from procrastination, of course. This afternoon, I planned to finish editing a piece. But, it looked nice outside so I first went for a walk and then took a shower. Then, I sat down, finished my editing, and submitted the work. Ahead of deadline, again. It feels good.

What do you do to beat procrastination? And, what horrifying mistakes have I made in this post? Please let me know in the comments below.

Procrastination, Self Esteem and Freelance Writing


Welcome to The Anonymous Blog. My name is Kris. I’m not trying to be anonymous for any mysterious reason. It’s simply part of an experiment. You see, I’ve had some bad luck in the job market, despite an excellent education and excellent qualifications. Right now, I live in poverty. Not the kind of poverty where I can only buy two pairs of pants instead of three, but real, stomach-growling, shivering, terrifying poverty. I didn’t grow up poor, and I never expected I would be. It has been rough for a long time. But, at the beginning of the year, something changed…

I decided to work from home.

You’ve probably seen all those “Work from Home” ads, where you can make $3,000 a week doing apparently nothing. I’ve seen hundreds, and never followed a single link. I still have no idea what they are about. They sound too good to be true, and I don’t want to end up on a mailing list that never lets me go. Any job requiring me to spam Facebook is a job I want nothing to do with. And, even if I wanted to put money into selling something like Tupperware, I wouldn’t have the money to get started.

But, I know it can be done. Even before “the internet”, my aunt made her way as a successful freelance journalist. I’ve watched her career over the years with mild interest. I never thought it was the job for me, but she has a lot of freedom, and she seems financially secure. Friends I’ve made here and there, too, have established, successful online careers. Some work for themselves, some don’t. Acquaintances without half the qualifications I have are killing it in their chosen online fields. So clearly it can be done.

But how?

I’ve decided to become a blogger and a writer. My background is in liberal arts, I have a few style guides on hand, and that’s about it. Beyond that, I’m going to learn as I go. I’m not going to pay anyone $37 for a scummy ebook. I’ve done that before, and will not make the same mistake again. I’m not signing up for survey sites, or sites guaranteeing leads, followers and fame, or even a temp service. Instead, I am going to stumble around and make mistakes. I’m going to talk to people. I plan to utilize plenty of free resources in this undertaking. And of course I will share it all with you.

Right now, I’m overwhelmed, intimidated and scared. I’m reading, writing, and absolutely devouring all the information I can find. Already, I know writing and blogging is not a job for everyone. It can be mysterious and frightening and overwhelming and stressful. Fortunately, I know it’s the right job for me. I’m a strong writer, and I’ve honed my skills through years of education and practice, both personally and professionally. I’ve been online and building websites since 1995.

I’ve already spent some time working from home, especially as a product tester. I haven’t earned any money yet, but it’s been satisfying. Today, though, I got my first paying gig through a site called Upwork. I created a profile there about 24 hours ago, so I know very little about it. But, getting that contract was a sign that it’s time to start documenting to journey.

I want to take you on this journey with me.

I’m going to share my thoughts, hopes, and fears with you as I become a writer. I’m going to tell you all the tips and tricks I’ve learned. I’m going to share my successes and failures with you. I’m going to post everything. Not because I love sharing everything about my life, but because I’m skeptical.

Yes, I’m skeptical. I still feel like working from home is too good to be true. And that’s where my anonymity comes in. I don’t want this blog linked to my other writing projects, or my Amazon profile, or my former career. Instead, I’m going to build it organically. No advertising, no paying for followers, no ghostwriters. Everything you see here will be built through reading, writing and commenting on other blogs and social media sites.

If you’re reading this, I’ve already been successful.

You found my little place on the internet, and you want to know what it’s all about. I hope you’ll stick around to find out. Over the coming weeks, months and years, this site will become a valuable resource for others who want to start careers as bloggers or writers. This site is starting from scratch, as a free WordPress site with no budget. My career is starting from scratch, too. I have $8 in my bank account, so there’s really nowhere to go but up. Wherever my career goes from here, it’s going to develop naturally, without me taking a single masterclass or paying for any information.

Thanks for joining me. I look forward to seeing you soon.